Key West Day Sail on Schooner America 2.0

Sail past Key West landmarks on a 105-ft schooner while enjoying complimentary soft drinks and expert crew narration.

From$56/ person

Duration

1.5 hrs

Ideal For

20-30 people

Includes

1.5-hour sail, Soda and water

Highlights

Glide across emerald Key West waters on the 105-ft Schooner America 2.0. Enjoy authentic sailing as the crew shares stories of local history and marine life.

Spot dolphins and other wildlife in their natural habitat
Hear live narration about Key West history and ecology
View Mallory Square, Sunset Pier and Sand Key Lighthouse from the water
Help hoist the sails or take a turn at the helm
Relax on teak decks with complimentary soda and water

What's Included

1.5-hour sail aboard Schooner America 2.0
Complimentary soda, juice and water

Things to know

Outside alcoholic beverages are not permitted. Check in at the ticket booth 30 minutes before departure; late arrivals may miss the boat.

FAQs

Q: Do I need a ticket for my young child?

A: All passengers require a ticket, but infants under 2 sail free.

Q: Can I bring my own food or drinks?

A: You may bring your own food. Outside alcohol is not permitted. Alcoholic drinks can be purchased on board or during booking.

Q: Is the schooner wheelchair accessible?

A: No, America 2.0 is not wheelchair-accessible.

Q: What should I wear and bring?

A: Wear comfortable clothing and footwear and bring a light jacket. Sunscreen is recommended and also available on board.

Q: Is there parking, where? And how much is it?

A: Parking in Key West is extremely limited. There are several local municipal parking lots near the Historic Key West Bight area, and additional information (including lot options and directions) will be provided after you purchase your tickets.

Q: Is there a bathroom on the boat?

A: Yes. The boat has two bathrooms, called marine heads, and they are accessible at all times. The Captain will explain how to use them once you are on board.

Cancellation policy

Free cancellation or reschedule up to 24 hours before departure. Day-of cancellations are non-refundable. Operator may cancel for unsafe weather; if this occurs you can reschedule or receive a full refund.

Meeting location

202R William Street, Key West FL, 33040

Experience provided by Classic Harbor Line - Key West

Handpicked for you, so you can book with confidence

Best local prices
Flexible cancellation
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Each booking directly supports small businesses in our community.

Key West Day Sail on Schooner America 2.0

Sail past Key West landmarks on a 105-ft schooner while enjoying complimentary soft drinks and expert crew narration.

From$56/ person

Duration

1.5 hrs

Ideal For

20-30 people

Includes

1.5-hour sail, Soda and water

Highlights

Glide across emerald Key West waters on the 105-ft Schooner America 2.0. Enjoy authentic sailing as the crew shares stories of local history and marine life.

Spot dolphins and other wildlife in their natural habitat
Hear live narration about Key West history and ecology
View Mallory Square, Sunset Pier and Sand Key Lighthouse from the water
Help hoist the sails or take a turn at the helm
Relax on teak decks with complimentary soda and water

What's Included

1.5-hour sail aboard Schooner America 2.0
Complimentary soda, juice and water

Things to know

Outside alcoholic beverages are not permitted. Check in at the ticket booth 30 minutes before departure; late arrivals may miss the boat.

FAQs

Q: Do I need a ticket for my young child?

A: All passengers require a ticket, but infants under 2 sail free.

Q: Can I bring my own food or drinks?

A: You may bring your own food. Outside alcohol is not permitted. Alcoholic drinks can be purchased on board or during booking.

Q: Is the schooner wheelchair accessible?

A: No, America 2.0 is not wheelchair-accessible.

Q: What should I wear and bring?

A: Wear comfortable clothing and footwear and bring a light jacket. Sunscreen is recommended and also available on board.

Q: Is there parking, where? And how much is it?

Q: Is there a bathroom on the boat?

A: Yes. The boat has two bathrooms, called marine heads, and they are accessible at all times. The Captain will explain how to use them once you are on board.

Cancellation policy

Review summary

4.9

Excellent

417 reviewsGoogle Maps

Classic Harbor Line delivers what most travelers dream about when visiting Key West: a gorgeous sailing experience with attentive crew, free-flowing drinks, and those famous sunsets everyone talks about. The sunset cruises seem to be the most popular option, and reviewers consistently rave about the whole package. You're not just getting a boat ride—expect fresh appetizers like shrimp cocktail, veggie platters, cheese and crackers, plus brownies for dessert. The crew gets mentioned by name constantly (Janet, Dan, Brad, Rae, Chelsea, Victoria), which tells you something about how memorable they make the experience. People appreciate the local history commentary during the sail, the smooth sailing even for families with young kids, and the genuinely friendly vibe on board. The America 2.0 schooner itself is described as beautiful and well-maintained. That said, there's one cautionary tale worth noting. While the overwhelming majority had flawless experiences, one family reported last-minute cancellations that derailed their plans entirely. It's a single complaint among overwhelmingly positive feedback, but it's the kind of thing that matters when you're coordinating vacation activities. For what it's worth, everyone else found the crew professional, accommodating, and reliable. Whether you're celebrating something special like a wedding or just want a chill evening on the water to destress, this seems to be one of those experiences that genuinely lives up to the hype. The moonlight sails also get love if you want something different from the sunset crowd.

What people are saying

Had a great time time with Classic Harbor Line in Key West! They were super accommodating for our 4 year old on the sunset cruise! The food and drinks were amazing! Looking forward to another amazing sailing experience with the world class crew soon. Glad we could enjoy the sunset cruise before the crew takes the boat to NYC for the summer!